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the intermediate positively charged nitrogen is being supplied by large electron clouds coming from both sides, i.e., the intermediary triple bonds with the other N that is attached to a conjugate base (that's why it is a diazonium salt) and the pi electron cloud from the benzene ring.... this makes the aromatic diazonium salt much more stable

on the other hand, the intermediate positively charged nitrogen is much less stable due to a weak van der waals and london forces coming from the aliphatic alkyl chain although the intermediary triple bonds of another nitrogen is near-by.

thus, it is the large pi electron cloud of the aromatic ring which stabilies the positively charged nitrogen of the diazonium salt

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12y ago
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11y ago

Aromatic diazonium salts are resonance stabilized and hence are more stable than the highly unstable aliphatic diazonium salts(which release N2 and ROH).

However the aromatic diazonium salts are very stable for a short period of time.

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13y ago

because of dispersal of +ve charge on the benzene ring due to resonance.

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Q: Why diazonium salts of aromatic amines are more stable than those of aliphatic amines?
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Why aromatic diazo compounds are more stable than aliphatic diazo compounds?

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